Proactive assistant

Proactive check-ins

Caddy notices relevant changes and texts before you ask, with the context and next step you need.

CaddyA changed deadline

The launch checklist in Linear moved from Friday to Wednesday. Your prep reminder is still set for Thursday. Want me to move it up?

Move my prep reminder up to tomorrow morning

The problem

Important changes live across too many tools, so you often only notice them after the window to act has passed.

How Caddy helps

Watch connected Gmail, Calendar, Slack, and Linear activity for meaningful changes.
Deliver user-created reminders at the time you asked for them.
Text a short explanation of what changed and why it matters.
Suggest a useful next step while keeping sensitive actions behind approval.

Why Caddy is different

A useful check-in arrives at the right time, explains why it matters, and gives you a clear next step. You decide which sources Caddy can use, what deserves a text, and whether any sensitive action should happen.

Caddy in action

CaddyA scheduled reminder

Quick reminder to send Jordan the final numbers before the 4:30 review

Thanks, I am doing it now

CaddyAn important message

Maya sent an urgent Slack message about the proposal and needs your review before 2. Want me to draft a reply?

Draft a reply saying I can review it by 2

What the workflow looks like

1
Connect the tools that hold the updates you care about or set a reminder in Messages.
2
Tell Caddy which people, changes, deadlines, or tasks deserve your attention.
3
Caddy texts when a matching update or scheduled reminder needs you.
4
Reply with what to do next and approve sensitive actions before they happen.

Texts to try

“Text me whenever a content deadline changes”
“Tell me when you notice something that you can automate”
“Check in when an important follow-up looks like it is slipping”

Common scenarios

Get a useful text before you ask

Caddy brings a reminder or connected-app change into the same iMessage thread where you already ask for help.

Related: AI assistant in iMessage

Keep the bigger picture in view

Use a morning brief for the shape of the day and proactive check-ins for important changes that happen later.

Related: Daily brief

Catch an important message

Tell Caddy which senders or topics matter so an urgent email can reach you without the rest of the inbox noise.

Related: Important email alerts by text

Best ways to use it

Start with a specific person, deadline, project, or reminder instead of every update.
Tell Caddy when a check-in was not useful so you can narrow the rule.
Disconnect a source or ask Caddy to stop proactive messages whenever you want less noise.

Frequently asked questions

What can trigger a proactive check-in?

A scheduled reminder or a meaningful change in a connected Gmail, Google Calendar, Slack, or Linear account can trigger a check-in.

Can I control which apps Caddy checks?

Yes. You choose which apps are connected and can disconnect them at any time.

Will proactive check-ins get noisy?

Start with specific people, projects, deadlines, or reminders. You can tell Caddy what was not useful and narrow the rule whenever you want.

Can I turn proactive messages off?

Yes. You can ask Caddy to stop proactive messages without removing the reminders and routines you created separately.

Will Caddy take action without asking?

A check-in can explain the issue and prepare a next step, but Caddy asks before sensitive actions such as sending a message or changing calendar details.